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Novel 2, 4-Methanoadamantane-Benzazepine by a Domino Photochemistry of N-(1-adamantyl)phthalimide


Basarić, Nikola; Horvat, Margareta; Mlinarić-Majerski, Kata; Zimmermann, Elmar; Neudörfl, Jörg; Griesbeck, Axel G.
Novel 2, 4-Methanoadamantane-Benzazepine by a Domino Photochemistry of N-(1-adamantyl)phthalimide // Organic Letters, 10 (2008), 18; 3965-3968 doi:10.1021/ol801362x (međunarodna recenzija, članak, znanstveni)


Naslov
Novel 2, 4-Methanoadamantane-Benzazepine by a Domino Photochemistry of N-(1-adamantyl)phthalimide

Autori
Basarić, Nikola ; Horvat, Margareta ; Mlinarić-Majerski, Kata ; Zimmermann, Elmar ; Neudörfl, Jörg ; Griesbeck, Axel G.

Izvornik
Organic Letters (1523-7060) 10 (2008), 18; 3965-3968

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
2; 4-methanoadamantane-benzazepine; N-(1-adamantyl)phthalimide; domino phothochemistry

Sažetak
The photochemical reaction of N-(1-adamantyl)phthalimide (1) gives cleanly one product, the novel hexacyclic benzazepine derivative of 2, 4-methanoadamantane 2. Its structure was characterized by spectroscopic methods and X-ray analysis and represent the first example of the 2-azahexacyclo[8.7.1.11, 4.04, 9.011, 16.012, 18]nonadeca-4, 6, 8-triene skeleton. The product is formed by a domino process of two consecutive excited state intramolecular hydrogen transfer reactions. Base hydrolysis of the benzazepine 2 gives in high yield the keto derivative of the 1, 2-substituted adamantane ε -amino acid 3.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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